Highly Efficient Nano-Catalysts Using Activated Carbon as a Support for One-Step Oxidation of Cyclohexane to Adipic Acid

Abstract:

A new route to substitute for the traditional two-step method for adipic acid production has been investigated. Supported nano metal catalysts Au/C and Co/C were prepared and used for liquid phase oxidation of cyclohexane to adipic acid with oxygen as an oxidant. These catalysts were characterized by XRD, TEM and ICP-AES. The reactions were carried out in an autoclave with solvent and radical initiator at 373~423K and 1.5 MPa. Au/C (1.25%) was found to be a highly efficient catalyst for the oxidation of cyclohexane with a high conversion (44.93%) of cyclohexane and more than 54.85% selectivity to adipic acid. It is indicated that there was a potential application prospect for the nano-catalysts in one-step oxidation of cyclohexane to adipic acid.

• Periodical: Key Engineering Materials (Volumes 562-565)
• Pages: 754-759
• DOI: https://doi.org/10.4028/www.scientific.net/KEM.562-565.754
• Online since: July 2013
• Authors: Huan Dai, Ming Qiao Zhu, Wei Li, Zhang Fa Tong
• Keywords: Adipic Acid, Cyclohexane, Nanocatalyst, Oxidation

References

[1] B. Hereijgers and B. Weckhuysen, Aerobic oxidation of cyclohexane by gold-based catalysts: new mechanistic insight by thorough product analysis, J. Catal., 207 (2010) 16-25.

DOI: 10.1016/j.jcat.2009.12.003

[2] U.Schuchardt, D. Cardoso, R. Sercheli, Cyclohexane oxidation continues to be a challenge, Appl. Catal. A., 211 (2001) 23-26.

[3] K.Yu, R. Hummeida, A. Abutaki and S. Chi, One-step catalytic cyclohexane oxidation to adipic acid using molecular oxygen, Catal. Lett., 111 (2006) 51-55.

DOI: 10.1007/s10562-006-0129-4

[4] Y. Yuan, H. Ji, Y. Chen, Y. Han, X. Song, Y. She and R. Zhong, Oxidation of cyclohexane to adipic acid using Fe−porphyrin as a biomimetic catalyst, Org. Pro. Res., 8 (2004) 418-420.

DOI: 10.1021/op049974s

[5] I. Hermans, P. Jacobs, J. Peeters, The formation of byproducts in the autoxidation of cyclohexane, Chem. Eur. J., 13 (2007) 754-757.

DOI: 10.1002/chem.200601242

[6] C. Della Pine, E. Falletta, L. Prati, M. Rossi, Selective oxidation using gold, Chem. Soc. Rev., 37 (2008) 2077-2080.

DOI: 10.1039/b707319b

[7] A.S.K. Hashmi, G.J. Hutchings, Gold catalysis, Angew. Chem. Int. Ed., 45 (2006) 7896-7899.

[8] G.C. Bond, D.T. Thompson, Catalysis by gold, Catal. Rev-Sci. Eng., 41 (1999) 319-321.

[9] K. Sankar, G. Thomas J. M., Mechanistic insights into the conversion of cyclohexene to adipic acid by H2O2 in the presence of a TAPO-5 catalyst, Angew.Chem., 39 (2000) 2313-2316．

[10] C.S. Yao, H. Weng, Liquid-phase cooxidation of cyclohexane and cyclohexanone over supported cerium oxide catalysts, Ind Eng Chem Res., 37 (1998) 2647-2653.

DOI: 10.1021/ie970790u

[11] G.M. Lü, R. Zhao, G. Qian, Y.X. Qi, X.L. Wang, J.S. Suo, A highly efficient catalyst Au/MCM-41 for selective oxidation cyclohexane using oxygen, Catal. Lett., 97 (2004) 115-119.

DOI: 10.1023/b:catl.0000038571.97121.b7

[12] R. Zhao, D. Ji, G.M. Lü, G. Qian, L. Yan, X.L. Wang, J.S. Suo, A highly efficient oxidation of cyclohexane over Au/ZSM-5 molecular sieve catalyst with oxygen as oxidant, Chem. Commun., 7 (2004) 904-907.

DOI: 10.1039/b315098d

[13] L.X. Xu, C.H. He, M.Q. Zhu, S. Fang, A highly active Au/Al2O3 catalyst for cyclohexane oxidation using molecular oxygen, Catal. Lett., 114 (2007) 202-206.

DOI: 10.1007/s10562-007-9058-0

[14] L.X. Xu, C.H. He, M.Q. Zhu, K.J. Wu, Y.L. Lai, Surface stabilization of gold by sol-gel post-modification of alumina support with silica for cyclohexane oxidation, Catal. Commun., 9 (2008) 816-820.

DOI: 10.1016/j.catcom.2007.09.005

[15] L.X. Xu, C.H. He, M.Q. Zhu, K.J. Wu, Y.L. Lai, Silica-supported gold catalyst modified by doping with titania for cyclohexane oxidation, Catal. Lett., 118 (2007) 248-251.

DOI: 10.1007/s10562-007-9178-6

[16] J. Zhao, M.Q. Zhu, J.J. Chen, Y.Y. Yang, Y. Tang, Cyclohexane oxidation catalyzed by Au/MxOy/Al2O3 using molecular oxygen, Adv. Mat. Res., 233 (2011) 254-259.

[17] H. Yu, F. Peng, J. Tan, X. Hu, H. Wang, J. Yang, and W. Zheng, Selective catalysis of the aerobic oxidation of cyclohexane in the liquid phase by carbon nanotubes, Angew. Chem., 10 (2010) 3978-3982.

DOI: 10.1002/anie.201007932